Water → HCID 70144159, compound

HRID 496071Notes

Reaction equation

HRID 496071 reaction equation
[BH4-].[Li+].[C:3]([O:7][C:8]([N:10]([CH3:19])[C:11]1([CH2:14][C:15](OC)=[O:16])[CH2:13][CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[OH:16][CH2:15][CH2:14][C:11]1([N:10]([CH3:19])[C:8](=[O:9])[O:7][C:3]([CH3:4])([CH3:6])[CH3:5])[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 4148881Lithium borohydrideHCID 59620515HCID 59620515, compound

Product 1

HCID 70144159HCID 70144159, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Over 20 minutes, 20 ml of 2M lithium borohydride in tetrahydrofuran is poured, at 20° C., into a mixture containing 4.86 g of the product obtained in Step 4 and 20 ml of tetrahydrofuran. After stirring for 20 hours at ambient temperature and then for 1 hour at reflux, the mixture is cooled to 5° C. and then hydrolysed using a mixture containing 8 ml of water and 4 ml of 10% aqueous sodium carbonate solution. The aqueous phase is extracted several times with ether. After customary treatment, chromatography of the residue over silica gel (CH2Cl2/tetrahydrofuran: 98/2) allows the expected product to be isolated (liquid).

Workup

  1. temperaturefor 1 hour at reflux
  2. temperaturethe mixture is cooled to 5° C.
  3. extractionThe aqueous phase is extracted several times with ether
  4. customto be isolated (liquid)

Sources & evidence

ORD record
ord-f186cfb404d144c694c81fdf8916f790
Source dataset
uspto-grants-2005_09
Patent number
US06943184B2

Reaction notes

Loading…